Month: February 2021

These common heterocyclic compound, 54149-17-6, name is 1-Bromo-2-(2-methoxyethoxy)ethane, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Formula: C5H11BrO2

[0917] To a cooled (0 C.) suspension ofdry NaH (0.512 g,21.4 mmol) in anhydrous DMF (10 mL) under an Argonatmosphere, a solutionof4-bromophenol (3.11 g, 17.8mmol)in anhydrous DMF (20 mL) was added dropwise over 2-3min. The mixture was stirred at oo C. for 10 min and thenallowed to warm to rt over 30 min. To the resulting whitesuspension was added 1-bromo-2-(2-methoxyethoxy)ethane(2.66 mL, 19.6 mmol) dropwise over 2 min and the mixturewas stirred at rt for 30 min and then at 65 C. for 1.5 h. Aftercooling to rt, the mixture was concentrated under reducedpressure to an oily suspension, diluted with brine (80 mL),and the mixture was extracted with EtOAc (3×60 mL). Thecombined extracts were washed with brine (2×25 mL), driedover Na2 S0 4 , filtered, and concentrated to give compound85a as a mobile, pale amber-colored oil, used inthe following reaction without further purification. Mass spectrum (LCMS,ESI pos.): Calcd. for C 11 H 15Br03 , 275.0/277.0 (M+H).found 275.2/277.1

The synthetic route of 1-Bromo-2-(2-methoxyethoxy)ethane has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA, NV; Player, Mark R.; Meegalla, Sanath K.; Illig, Carl R.; Chen, Jinsheng; Wilson, Kenneth J.; Lee, Yu-Kai; Parks, Daniel J.; Huang, Hui; Patel, Sharmila; Lu, Tianbao; US2014/364414; (2014); A1;,
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Related Products of 589-10-6, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 589-10-6, name is (2-Bromoethoxy)benzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: Chlorosulfonic acid (20.00 mmol) was added dropwise to an ice-salt bath solution of the appropriate bromoalkoxyphenyl (1-3) (10.00 mmol) dissolved in dichloromethane (25 ml) at -10 C. After stirring for 2 h, the reaction mixture was allowed to warm to room temperature, and was stirred for an additional hour. The reaction mixture was then poured into 200 g of cracked ice and extracted with dichloromethane. The organic layer was washed with brine, dried over anhydrous sodium sulfate and filtered. The solvent was removed under reduced pressure to afford the corresponding 4-(bromoalkoxy)benzenesulfonyl chloride derivatives (4-6).

The synthetic route of (2-Bromoethoxy)benzene has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ceras, Javier; Cirauqui, Nuria; Perez-Silanes, Silvia; Aldana, Ignacio; Monge, Antonio; Galiano, Silvia; European Journal of Medicinal Chemistry; vol. 52; (2012); p. 1 – 13;,
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Synthetic Route of 102503-23-1, The chemical industry reduces the impact on the environment during synthesis 102503-23-1, name is 1-(2,4-Dimethoxyphenyl)-N-methylmethanamine, I believe this compound will play a more active role in future production and life.

General procedure: N-(2,4-dimethoxybenzyl)-N-methyl-3-phenylprop-2-yn-1-amine (5a). CuI (20 mg, 0.10 mmol) was added to a solution of phenylacetylene(510.6 mg, 5.0 mmol), HCHO (36% aq., 2 mL),N-methyl(2,4-dimethoxybenzyl)amine (1.09 g, 6.0 mmol) in DMSO (10.0mL). The resulting yellow green solution was stirred at room temperatureovernight and then diluted with H2O (10 mL), extracted with Et2O (15 mL x 3). The combined extractswas washed with H2O (2 x), brine (2 x) respectively, dried over Na2SO4, filtered, concentrated. Theresultant yellow oil was purified through flash column chromatography (silica gel, EtOAc/Hex = 1:6 to1:3) to give the product (5a, 1.14 g, 96%).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 1-(2,4-Dimethoxyphenyl)-N-methylmethanamine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Yang, Miao; Odelberg, Shannon J.; Tong, Zongzhong; Li, Dean Y.; Looper, Ryan E.; Tetrahedron; vol. 69; 27-28; (2013); p. 5744 – 5750;,
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Reference of 450-88-4,Some common heterocyclic compound, 450-88-4, name is 1-Bromo-4-fluoro-2-methoxybenzene, molecular formula is C7H6BrFO, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

8.4 g of 1-bromo-4-fluoro-2-methoxybenzene obtained by Production example 89 was dissolved in 200 mL of dichloromethane, added under nitrogen atmosphere at 0C with 21 mL of titanium tetrachloride and 5.6 mL of dichloromethylmethylether, and stirred at room temperature for 4 hours and 30 minutes. The reaction solution was slowly poured into ice water, and extracted twice with diethyl ether. The organic layer was washed successively with water, saturated aqueous sodium hydrogen carbonate and water, and then dried over magnesium sulfate. The solvent was evaporated, to afford 9.44 g of the title compound as white crystals.1H-NMR ( 400 MHz, CDCl3 ) delta 3.97 ( 3H, s ), 6.67 ( 1H, d, J = 12.0 Hz ),8.05 ( 1H, d, J = 7.6 Hz ), 10.15 ( 1H, s )

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Bromo-4-fluoro-2-methoxybenzene, its application will become more common.

Reference:
Patent; Eisai Co., Ltd.; EP1510516; (2005); A1;,
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Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 74654-07-2, name is 2-(2-(2-Methoxyethoxy)ethoxy)ethanamine, A new synthetic method of this compound is introduced below., Quality Control of 2-(2-(2-Methoxyethoxy)ethoxy)ethanamine

A solution of cyanoacetic acid (621 mg, 7.3 mmol) in anhydrous DCM (15 mL) was cooled to 0C. Separately, a solution of hydroxybenzothiazole (HOBt) (1.48 g, 10.97 mmol) and 2-(2-(2-methoxyethoxy)ethoxy)ethanamine (A2, 1.79 g, 10.97 mmol) was prepared in DCM (10 mL); this solution was then added dropwise to the cooled solution of cyanoacetic acid. The resulting solution was allowed to stir for 10 minutes at 0C, upon which l-ethyl-3-(3- dimethylaminopropyl)carbodiimide (EDC) (2.1 g, 10.97 mmol) was added in one portion and the reaction stirred under argon at 0C for 12 hours. The reaction was then concentrated and purified by silica gel chromatography (0-2% MeOH/DCM) to obtain 2-cyano-N-(2-(2-(2- methoxyethoxy)ethoxy)ethyl)acetamide A3 as a yellow oil in 83% yield.

The synthetic route of 74654-07-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AMYDIS DIAGNOSTICS; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; YANG, Jerry; THEODORAKIS, Emmanuel, A.; SARRAF, Stella; WO2015/143185; (2015); A1;,
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Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 89282-70-2, name is 2-Methoxy-2-methylpropan-1-amine, A new synthetic method of this compound is introduced below., SDS of cas: 89282-70-2

Hydrochloric acid generated from concentrated sulfuric acid and sodium chloride (or from dripping of concentrated hydrochloric acid over concentrated sulfuric acid), was bubbled through a solution of MIBA (298.73 g, 97.0% (GC), 2.81 mmol) in hexanes (7160 mL) until most of the forming MIBAHCl solubilizes. The solvent was carefully removed by rotary evaporation under reduced pressure. The obtained product, a white solid, was dried under high vacuum and triturated in hot hexanes (2860 mL). MIBAHCl was filtered off under a blanket of argon and yielded as a white solid (386.88 g, 99.0% (GC), 98% yield). The title compound is highly hygroscopic and should be stored in a dessicator. m.p.: 121-123 C.; TLC Rf 0.5 (90:9.75:0.25 CH2Cl2/CH3OH/NH4OH, sample diluted in a mixture of 1 mL:1 drop CH3OH/28% NH4OH, detection with ninhydrine spray); FTIR(KBr): 3426, 2978, 2692, 2596, 2008, 1618, 1499, 1476, 1396, 1374, 1329, 1264, 1206, 1177, 1096, 1057, 1013, 949, 871, 841, 720 cm-1; 1H (600 MHz, CDCl3): delta 1.20 (s, 6H, 2 CH3), 2.91 (q, 2H, J=5.9 Hz, CH2), 3.14 (s, 3H, OCH3), 8.21 (br s, 3H, NH3+); 13C-NMR (151 MHz, CDCl3): delta 22.5 (2 CH3), 47.9 (CH2), 49.5 (OCH3), 72.0 (C).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; DRAXIS Specialty Pharmaceuticals Inc.; US2008/102028; (2008); A1;,
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Electric Literature of 5414-19-7, The chemical industry reduces the impact on the environment during synthesis 5414-19-7, name is 1-Bromo-2-(2-bromoethoxy)ethane, I believe this compound will play a more active role in future production and life.

TP5 – To 200 mg (0.984 mmol) of (R)-6-(4-aminophenyl)-5-methyl-4,5- dihydropyridazin-3(2H)-one dissolved in 1 mL of DMF was added 250 (2.00 mmol) of bis (2-bromoethyl) ether and 400 mg of K2CO3 and the mixture was stirred overnight at 60 C. The next day another 250 mu^ of bis (2-bromoethyl) ether and 170 mg of K2CO3 was added. After 3 h, EtOAc and water were added, the water was rinsed with EtOAc, the combined EtOAc washes were dried and concentrated. Chromatography with 0-4% MeOH in CH2C12 yielded 125 mg of product (46%). XH NMR (300 MHz, CDC13) delta 8.61 (s, 1H), 7.68 (d, J= 8.8, 2H), 6.92 (d, J= 8.8, 2H), 3.99 – 3.76 (m, 4H), 3.44 – 3.31 (m, 1H), 3.29 – 3.22 (m, 4H), 2.70 (dd, J= 6.7, 16.8, 1H), 2.46 (d, J= 16.7, 1H), 1.24 (d, J= 7.3, 3H). 13C NMR (75 MHz, CDC13) delta 166.64, 154.05, 152.18, 127.10, 125.33, 1 14.73, 66.69, 48.33, 33.93, 27.94, 16.36. MS: 274 (M + 1). Anal. Calcd. for C15H19N3O2: C, 65.91; H, 7.01 ; N, 15.37; Found. 65.81, H, 6.66, N, 15.26.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 1-Bromo-2-(2-bromoethoxy)ethane, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; THE BROAD INSTITUTE, INC.; DANA FARBER CANCER INSTITUTE, INC.; LEWIS A., Timothy; MUNOZ, Benito; DE WAAL, Lucian; GREULICH, Heidi; MEYERSON, Matthew; GECHIJIAN, Lara Nicole; WO2014/164704; (2014); A2;,
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Electric Literature of 75148-49-1, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 75148-49-1, name is 3-Bromobenzaldehyde Diethyl Acetal, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: One equiv. of protected hydrazine was dissolved/suspended in EtOH containing 10% water (approx. 5 ml per 1 mmol of protected hydrazine), 1.05 eq of benzaldehyde acetal was added, followed by the addition of 0.05 equiv. of TsOH in an ethanolic solution (10 mg of TsOH per 0.5 ml of EtOH). The obtained reaction mixture was refluxed and monitored by TLC (silica gel) until full conversion of the starting material was observed. Ethyl acetate/light petroleum mixtures or pure ethyl acetate were used as TLC eluents. After completion of the reaction the solvent was removed under reduced pressure, approx. 15 ml of toluene was added to the residue and the solvent was again removed under reduced pressure. The obtained crude hydrazone was dissolved in commercial stabilized THF (approx. 4 ml per 1mmol of hydrazone), the flask was flushed with argon and 3 equiv. of 1M BH3-THF complex was added at room temperature, followed by 3 hours of stirring. The progress of the reaction was checked by TLC and if some unreacted hydrazone was left, stirring was continued for an additional 45 min. After thefull conversion of hydrazone EtOH (10 ml) was added to the reaction mixture (Caution: Liberation of hydrogen) and the obtained mixture was refluxed for 1 hour. After cooling to room temperature the solvent was removed under reduced pressure and the residue was dissolved in ethyl acetate, washed with saturated NaHCO3 solution, water and saturated NaCl solution. The aqueous phase was extracted twice with ethyl acetate, the extracts were washed with saturated NaCl solution, combined with the organic phase, dried over anhydrous Na2SO4 and evaporated to dryness. The residue was purified by column chromatography on silica gel by using ethyl acetate/light petroleum 1:1 or 1:2 mixtures or pure ethyl acetate as eluent. For the exact information about the eluent used for monitoring reaction progress and chromatographic purifications, see the Rf value for each compound.

The chemical industry reduces the impact on the environment during synthesis 3-Bromobenzaldehyde Diethyl Acetal. I believe this compound will play a more active role in future production and life.

Reference:
Article; Mastitski, Anton; Niinepuu, Siret; Haljasorg, Toiv; Jaerv, Jaak; Organic Preparations and Procedures International; vol. 50; 4; (2018); p. 416 – 423;,
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123652-95-9, name is (3-Fluoro-4-methoxyphenyl)methanamine, belongs to ethers-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. SDS of cas: 123652-95-9

General procedure: Spirothiazamenthane 3 (1.0 eq) was dissolved in toluene (0.1 M concentration) in a microwave vial and the solution was treated with amine (10 eq) and PTSA (20 mol %). This mixture was heated at 150 C using microwaves for 4 h. After cooling, the solvents were removed by evaporation and the resulting residue was taken up in 1:1 Et2O/2M NaOH. The layers were separated and the aqueous layer was extracted 2 ¡Á with Et2O. The organic layers were combined, dried over Na2SO4, filtered and concentrated. The resulting crude products were purified as described below. Variations in reaction conditions are also noted below.

The synthetic route of 123652-95-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Arns, Steve; Balgi, Aruna D.; Shimizu, Yoko; Pfeifer, Tom A.; Kumar, Nag; Shidmoossavee, Fahimeh S.; Sun, Sharon; Tai, Sheldon S.-H.; Agafitei, Olga; Jaquith, James B.; Bourque, Elyse; Niikura, Masahiro; Roberge, Michel; European Journal of Medicinal Chemistry; vol. 120; (2016); p. 64 – 73;,
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Application of 886762-08-9, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 886762-08-9, name is 5-Bromo-2-(trifluoromethoxy)aniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

N-(5-bromo-2-(trifiuoromethoxy)phenyl)acrylamide (2): To a solution of 5-bromo- 2-(trifiuoromethoxy)aniline (1.2 g, 4.7 mmol) in dichloromethane (5.0 niL), diisopropylethylamine (727 mg, 5.64 mmol) and acryloyl chloride (382 mg, 4.22 mmol) were added at -78 C. The reaction mixture was allowed to stir at 0 C for 2 h. After completion of the reaction, the reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford 2 (1.4 g, 93%) as an off white solid. 1H NMR (400 MHz, DMSO-d6) : delta 5.79-5.80 (dd, J = 1.82 Hz, 10.2 Hz, 1H), 6.26-6.27 (dd, J = 1.8, 17.0 Hz, 1H), 6.61-6.63 (dd, J = 17.0 Hz, 1H), 7.38-7.40 (m, 2H), 8.28-8.29 (d, J = 2.3 Hz, 1H), 10.07 (brs, 1H). MS m/z (M+H): 310.45

The synthetic route of 5-Bromo-2-(trifluoromethoxy)aniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CELGENE AVILOMICS RESEARCH, INC.; ALEXANDER, Matthew David; MCDONALD, Joseph John; NI, Yike; NIU, Deqiang; PETTER, Russell C.; QIAO, Lixin; SINGH, Juswinder; WANG, Tao; ZHU, Zhendong; WO2014/149164; (2014); A1;,
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